Vinylglycine methyl ester

Intermolecular cyclopropanation reactions with ethyl diazoacetate have been employed for the construction of the cyclopropane-containing amino acid 7 (equation 25) Thus, rhodium(II) acetate catalysed decomposition of ethyl diazoacetate in the presence of d-cbz-vinylglycine methyl ester 5 afforded cyclopropyl ester 6 in 85% yield. Removal of the protecting group completed the synthesis of 7. Another example illustrating intermolecular cyclopropanation can be found in Piers and Moss synthesis of ( )-quadrone 8" (equation 26). Intermolecular cyclopropanation of enamide or vinyl ether functions using ethyl diazoacetate has also been used in the synthesis of eburnamonine 9", pentalenolactone E ester 10" and ( )-dicranenone A11" (equations 27-29). 

N-(BENZYL0XYCARB0NYL)-L-VINYLGLYCINE methyl ester (3>But nolc acid, 2>[[(phenylmethoxy)carbonyl]amino]-, methyl ester, (S)-)... 

Since protein and peptide syntheses are rapidly falling into the hands of organic chemists, four procedures to reach building blocks amino acids in the form of its /8-lactone Na-(BENZYLOXY-CARBONYL)-p-(PYRAZOH-YL)-L-ALANINE and the preparation of both /3-lactones, N-tert-BUTOXYCARBONYL-L-SERINE-p-LACTONE and the p-TOLUENESULFONIC ACID SALT OF (S)-3-AMINO-2-OXE-TANONE are described starting from N-tert-BUTOXYCARBONYL-L-SERINE. A useful S or R serine derivative, 1,1-DIMETHYLETHYL (S) or (R)-4-FORMYL-2,2-DIMETHYL-3-OXAZOLIDINECARBOXYLATEis described followed by the improved preparation of N-(BENZYLOXY-CARBONYD-L-VINYLGLYCINE METHYL ESTER, an important intermediate as well as an important substance in biological processes. 

N-(Benzyloxycarbonyl)-L-vinylglycine methyl ester 3-Butenoic acid, 2-[[(phenylmethoxy)carbonyl]amino]-, methyl ester, (S)- (10) (75266-40-9) N-(Benzyloxycarbonyl)-L-methionine methyl ester L-Methionine, N-[(phenylmethoxy)carbonyl]-, methyl ester (9) (56762-93-7)... 

Michael Carrasco, Robert J. Jones, Scott Kamel, H. Rapoport, and Thien Truong 29 N-(BENZYLOXYCARBONYL)-L-VINYLGLYCINE METHYL ESTER... 

In order to activate or enhance the activity of group III of the metabotropic glutamate receptors, new and potent phosphinic agonists were synthesized by Acher et al. in 2007 [54], Indeed, these presynaptic receptors inhibit the adenylate cyclase and the release process. y-Phosphinic acid derivative 49 is the key intermediate for the formation of compounds 51,52 and 53 (Scheme 7). Starting from a radical addition of hypophosphorous acid to the IV-CBz protected vinylglycine methyl ester 48, the phosphinic derivative compound 49 was obtained in 94%... 

Unsaturated a-Amino-acids.—A general route to a-vinyl-a-amino-acids is based upon Stork s approach to substituted glycines (see ref. 288 etc.) and uses the enolate of the Schiff s base formally derived from benzaldehyde and methyl a-aminocrotonate (Scheme 54). ° -Vinylglycine itself cannot be prepared by this method as addition of water to the intermediate anion gives pure E) starting material. a-Vinylalanine has been obtained in good yields by a somewhat different approach from the enolate of alanine methyl ester and rrans-phenyl-2-... 

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